Those important songs that help teen pop stars pivot into full-fledged adults.

Every week, a different FADER editor compiles a playlist to highlight a new release and give you a guide to that artist’s web of influences and peers. These Staff Selects live in our Spotify app, alongside GEN Fs from our archives and playlists for each issue. This week, Alex Frank talks about the songs that broke teen pop stars out of their molds.

There's nothing like having something to prove to motivate someone to make their best work. In that pivotal moment when a teen or tween pop star is trying to grow up and shed their acne to become a full-fledged adult celeb, they very often stretch to produce their best and most innovative work in an effort to be taken seriously. Though 2013 was, in part, a year of controversial teen behavior—Selena in Spring Breakers, Miley at the VMAS, Justin at Brazlian brothels—it was also the year that all three of them made the most interesting music of their entire careers. Here's a round-up of songs that teen idols made at pivot points in their careers. Though a few of the songs now sound ominous in the wake of their singers' public meltdowns, downward career trajectories and controversies, think of it as an inevitably awkward soundtrack to the very hard task of growing up.